EP2848303A2 - Procédé de refroidissement de matériaux structurels organométalliques poreux, procédé d'obtention d'aldéhyde à l'aide de matériaux structurels organométalliques poreux et procédé permettant de chauffer des matières structurantes organo-métalliques poreuses - Google Patents

Procédé de refroidissement de matériaux structurels organométalliques poreux, procédé d'obtention d'aldéhyde à l'aide de matériaux structurels organométalliques poreux et procédé permettant de chauffer des matières structurantes organo-métalliques poreuses Download PDF

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EP2848303A2
EP2848303A2 EP20140184282 EP14184282A EP2848303A2 EP 2848303 A2 EP2848303 A2 EP 2848303A2 EP 20140184282 EP20140184282 EP 20140184282 EP 14184282 A EP14184282 A EP 14184282A EP 2848303 A2 EP2848303 A2 EP 2848303A2
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framework materials
porous metal
organic framework
item
adsorbate
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English (en)
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EP2848303A3 (fr
EP2848303B1 (fr
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Takaiki Nomura
Takashi KOUZAKI
Takahiro KURABUCHI
Kazuhito Hato
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Panasonic Intellectual Property Management Co Ltd
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Panasonic Corp
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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/223Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material containing metals, e.g. organo-metallic compounds, coordination complexes
    • B01J20/226Coordination polymers, e.g. metal-organic frameworks [MOF], zeolitic imidazolate frameworks [ZIF]
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/08Copper compounds
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D53/00Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/02Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
    • B01D53/04Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography with stationary adsorbents
    • B01D53/0454Controlling adsorption
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30Processes for preparing, regenerating, or reactivating
    • B01J20/34Regenerating or reactivating
    • B01J20/3425Regenerating or reactivating of sorbents or filter aids comprising organic materials
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30Processes for preparing, regenerating, or reactivating
    • B01J20/34Regenerating or reactivating
    • B01J20/3441Regeneration or reactivation by electric current, ultrasound or irradiation, e.g. electromagnetic radiation such as X-rays, UV, light, microwaves
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/72Copper
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/1691Coordination polymers, e.g. metal-organic frameworks [MOF]
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2204Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208Oxygen, e.g. acetylacetonates
    • B01J31/2226Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2239Bridging ligands, e.g. OAc in Cr2(OAc)4, Pt4(OAc)8 or dicarboxylate ligands
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/37Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
    • C07C45/38Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/02Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41Preparation of salts of carboxylic acids
    • C07C51/412Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/14Monocyclic dicarboxylic acids
    • C07C63/15Monocyclic dicarboxylic acids all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
    • C07C63/241,3 - Benzenedicarboxylic acid
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/307Monocyclic tricarboxylic acids
    • FMECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F17STORING OR DISTRIBUTING GASES OR LIQUIDS
    • F17CVESSELS FOR CONTAINING OR STORING COMPRESSED, LIQUEFIED OR SOLIDIFIED GASES; FIXED-CAPACITY GAS-HOLDERS; FILLING VESSELS WITH, OR DISCHARGING FROM VESSELS, COMPRESSED, LIQUEFIED, OR SOLIDIFIED GASES
    • F17C11/00Use of gas-solvents or gas-sorbents in vessels
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D2253/00Adsorbents used in seperation treatment of gases and vapours
    • B01D2253/20Organic adsorbents
    • B01D2253/204Metal organic frameworks (MOF's)
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D2257/00Components to be removed
    • B01D2257/50Carbon oxides
    • B01D2257/504Carbon dioxide
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D2259/00Type of treatment
    • B01D2259/40Further details for adsorption processes and devices
    • B01D2259/40083Regeneration of adsorbents in processes other than pressure or temperature swing adsorption
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D53/00Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/32Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by electrical effects other than those provided for in group B01D61/00
    • B01D53/323Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by electrical effects other than those provided for in group B01D61/00 by electrostatic effects or by high-voltage electric fields
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/70Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/70Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
    • B01J2231/76Dehydrogenation
    • B01J2231/763Dehydrogenation of -CH-XH (X= O, NH/N, S) to -C=X or -CX triple bond species
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/10Complexes comprising metals of Group I (IA or IB) as the central metal
    • B01J2531/16Copper
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02CCAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
    • Y02C20/00Capture or disposal of greenhouse gases
    • Y02C20/40Capture or disposal of greenhouse gases of CO2
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/30Hydrogen technology
    • Y02E60/32Hydrogen storage
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/151Reduction of greenhouse gas [GHG] emissions, e.g. CO2

Definitions

  • R 5 X m (COOH) n or R 6 X m (N-R 7 R 8 ) n where m represents an integer of two or more, and each of R 5 , R 6 , R 7 and R 8 independently represents a hydrocarbon group which can be substituted with a substituent.
  • FIG. 9 shows examples of R 1 , R 2 , R 5 , and R 6 .
  • the hydrocarbon groups and the nitrogen-containing hydrocarbon groups shown in FIG. 9 can be substituted with a substituent.
  • the porous metal-organic framework materials is brought into contact with carbon dioxide to adsorb carbon dioxide onto the porous metal-organic framework materials.
  • the magnetic field or the electromagnetic field applied to the porous metal-organic framework materials allows a larger amount of carbon dioxide to be adsorbed onto the porous metal-organic framework materials.
  • the organic compound in the method for adsorbing carbon dioxide in a magnetic field, is not limited, as long as the organic compound has at least one functional group which is capable of forming at least two coordination bonds to the at least one metal ion. Not only a polar compound but also a non-polar compound may be used.
  • the method for cooling porous metal-organic framework materials is also divided into a method for cooling in an electric field and a method for cooling in a magnetic field.
  • an electric field or an electromagnetic field is applied to the porous metal-organic framework materials containing the adsorbates. This releases the adsorbates from the porous metal-organic framework materials. When the adsorbates are released from the porous metal-organic framework materials, the adsorbates draw heat from the porous metal-organic framework materials. In this way, the porous metal-organic framework materials are cooled. When the adsorbates are water, the drawn heat may be referred to as "vaporization heat". It is desirable that an electric power supply and two electrodes are used to apply the electric field. It is desirable that the electric power supply is an alternating-current source. In other words, it is desirable that an alternating-electric field is applied to the porous metal-organic framework materials. The porous metal-organic framework materials may be disposed between the two electrodes.
  • R-CH 2 OH is brought into contact with the porous metal-organic framework materials to oxidize at least a part of R-CH 2 OH. In this way, R-CHO is obtained.
  • an electric power supply and two electrodes are used to apply the electric field.
  • the electric power supply is an alternating-current source. In other words, it is desirable that an alternating-electric field is applied to the porous metal-organic framework materials.
  • the porous metal-organic framework materials may be disposed between the two electrodes.
  • FIG. 5 is a graph indicating the X-ray diffraction results of the porous metal-organic framework materials obtained in the example A4.
  • Table 1 shows the gas composition ratios of the gaseous mixtures which were measured before and after the electric fields were applied in the examples A1 - A5 and the comparative example A1.
  • Table 1 Gas composition ratio of the source gas Gas composition ratio of the gaseous mixture before an electric field was applied Gas composition ratio of gaseous mixture after an electric field was applied Example A1 3.7 4.0 4.3 Example A2 4.2 4.5 Example A3 4.0 4.5 Example A4 4.2 4.9 Example A5 4.2 4.6 Comparative example A1 4.2 4.2
  • the gas composition ratios of the gaseous mixtures after the electric fields were applied are higher than the gas composition ratios of the gaseous mixtures before the electric fields were applied. This reveals that the amount of carbon dioxide adsorbed onto the porous metal-organic framework materials is increased by bringing carbon dioxide into contact with the porous metal-organic framework materials under a condition where the electric field is applied to the porous metal-organic framework materials.
  • the inside of the container 202 was decompressed using a vacuum pump (not shown) connected through the outlet 204 until the inside of the container 202 had a pressure of not more than 1 Torr. At this point, the porous metal-organic framework materials had a temperature of 25 degrees Celsius.
  • the alternating-current source 103 was used to apply an AC voltage having a voltage of 1 volt and a frequency of 60Hz to the coil 201 for ten minutes.
  • the temperature of the porous metal-organic framework materials fell to 26 degrees Celsius. It was believed that this was because water contained as the adsorbates was released from the porous metal-organic framework materials by the action of the magnetic field.
  • the application of the AC voltage was stopped. After the application of the AC voltage was stopped, the temperature of the porous metal-organic framework materials was raised to 31 degrees Celsius. It was believed that this was because water was adsorbed again onto the porous metal-organic framework materials as the adsorbates.
  • the alternating-current source 103 was used to apply an AC voltage having a voltage of 1 volt and a frequency of 60Hz between the two electrodes 101 for ten minutes. Subsequently, a part of the air contained in the container 102 was extracted again. The extracted air was subjected to gas chromatography. As a result of the gas chromatography, the air extracted after the AC voltage had been applied contained acetaldehyde.
  • Air having an atmosphere temperature of 28 degrees Celsius and an ethanol density of 10 ppm was supplied to the container 202 through the inlet 205 until the air had a pressure of 760 Torr. Subsequently, a part of the air contained in the container 202 was extracted. The extracted air was subjected to gas chromatography. As a result of the gas chromatography, the air extracted at this point contained no acetaldehyde.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Analytical Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
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  • Carbon And Carbon Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
EP14184282.3A 2013-09-12 2014-09-10 Procédé de refroidissement des matériaux à squelette organométallique (mof) Active EP2848303B1 (fr)

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JP2013189189 2013-09-12
JP2013189188 2013-09-12

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EP2848303A2 true EP2848303A2 (fr) 2015-03-18
EP2848303A3 EP2848303A3 (fr) 2015-08-19
EP2848303B1 EP2848303B1 (fr) 2017-01-04

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US10427134B1 (en) * 2016-12-20 2019-10-01 The United States Of America As Represented By The Secretary Of The Army Enhancement of adsorption via polarization in a composite material
JP6638685B2 (ja) 2017-03-31 2020-01-29 トヨタ自動車株式会社 金属有機構造体とその製造方法
JP2019181452A (ja) * 2018-03-30 2019-10-24 パナソニックIpマネジメント株式会社 脱硫器、水素生成装置、および燃料電池システム
KR102780674B1 (ko) 2018-08-16 2025-03-12 커먼웰쓰 사이언티픽 앤 인더스트리알 리서치 오거니제이션 금속 유기 구조체 기반 물 포획 장치
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JP7694141B2 (ja) * 2021-05-19 2025-06-18 株式会社デンソー 二酸化炭素回収システム
CN113750917B (zh) * 2021-09-10 2024-05-03 刘建浩 一种高弹性耐高温气凝胶及其制备方法
CN116336691B (zh) * 2023-03-24 2026-03-17 西安交通大学 一种工质和载气可分离的电化学氨气压缩系统及方法

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US9309264B2 (en) 2016-04-12
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